


Almost Lost

by prettynialller



Category: Supernatural
Genre: Case Fic, Dean Winchester - Freeform, Distraught Dean Winchester, Established Relationship, F/M, Fluff, Human Castiel (Supernatural), Hurt Castiel (Supernatural), Hurt/Comfort, M/M, Parental Jody Mills, Protective Dean Winchester, Sam Winchester - Freeform, castiel - Freeform, castiel almost dies, claire novak - Freeform, eileen leahy - Freeform
Language: English
Status: In-Progress
Published: 2021-01-02
Updated: 2021-01-09
Packaged: 2021-03-12 10:07:21
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 5,471
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28508682
Author URL: https://archiveofourown.org/users/prettynialller/pseuds/prettynialller
Summary: It was supposed to be a small, easy, straightforward hunt. Just a small werewolf pack. They estimated about three at the most. They could handle that, right?It was supposed to be an easy hunt. But nothing ever goes as planned when it involves the Winchesters and now with their newly human, ex-angel friend, it only took minutes before shit got out of hand.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 8
Kudos: 17





	1. So Get This

“So get this,” Sam says as he strides into the war room, tablet in hand.

Dean and Cas are sat next to each other; Dean is halfway reading the article on his laptop and also engrossed in watching Cas as he is buried in a mound of books with a hot mug of tea in between his hands. Dean watches as Cas’s lips move silently as he reads along to the lore in front of him with the small lines in between his eyebrows in concentration.

Sam clears his throat, respectfully, signaling his entrance _once again._

Dean tears his eyes from Cas, clearing his throat, he lays his laptop onto the table in front of him, “Hey Sammy, you actually got something?”

They had been following up on a possible case in a small town in Virginia, researching for days, still stumped on what they possibly could be hunting. Five teenagers were reportedly kidnapped during the day and found weeks later completely torn to shreds. They’ve never heard or seen anything like it.

After the first few days of researching, they started doubting whether it was their kind of _thing_ or not. Each of them starting to get frustrated with the lack of information, evidence, and details around the incident. Each victim followed a totally different story. None of it was linking up.

Dean was especially frustrated, considering they just got back from a two-week-long vampire hunt in Colorado. A hunt that he regretfully got injured after getting a little big-headed and threatened two of the vampires at once. He admits that it was his fault and that he was a bit “reckless” as Cas had put it. But even so, he needed to rest, his back still tense and shoulders aching even after the countless hot steaming showers he’s taken, desperate for the hot water to calm the gnawing pain and muscle tears he had caused.

“Yeah, actually. I think we are hunting a small pack of werewolves.” Sam claims, sitting down across from the pair with his own mug of tea looking between them.

Cas finally looks up from his bundle of books, looking even more confused.

“Are you-?” He cuts himself off, frustratedly, “Are you _sure_? You say you _think_?” He closes the book in front of him roughly, hands rubbing at his temples.

“Well, honestly, I’m not so sure, but it’s the closest guess I have,” Sam says with a shrug.

“Seriously? Werewolves?” Dean grumbles, running a hand down his face.

A pack of werewolves is the last thing Dean wanted to hunt after their tricky vampire hunt just three days ago. He absolutely despises werewolves.

Cas doesn’t usually want to back down from a hunt, but he doesn’t know how to describe the anxieties he feels with this particular case, and he helps they listen to him just this once.

“Werewolves don’t even match up with the deaths. Sam, they were _shredded_ to pieces. The Bedford Sheriff said they barely were able to identify the bodies. The werewolves we hunt are usually linked up with missing hearts, not their whole body shredded beyond recognition. Does that sound like any normal werewolf to you?” Cas states.

Dean sits up at that because Cas does have a point. The bodies being shredded past recognition is quite a concern. He looks at Sam but stays quiet for a moment waiting for his brother to take the lead on this one.

“Guys-“ He cuts himself off, struggling to find the right words he wants to say. “This is all we got so far. I don’t think we will get much information without going out there and checking it out ourselves. We’ve done all we can from here; let’s get off our asses and go figure this out.” Sam looks between the two before turning to Cas specifically. “Cas, these are teenagers. Imagine if Claire wasn’t a hunter and this happened to her. You would want to know what the hell it was.”

Cas sucks in a deep breath at that. “Don’t even bring that possibility up.”

It’s no doubt that Cas is still protective of Jimmy Novak's daughter after everything she’s been through. He blames himself mostly for everything he’s caused. But Sam bringing that up as bait just to get him on board with this case is a low blow.

“Alright, alright, alright,” Dean pipes up between the two, shooting daggers at his brother before turning to Cas. “Cas, I hear you. It is strange, but I think Sammy is right. We can’t do much just sitting here.”

Cas locks eyes with Dean for a few moments. He hopes Dean can read his expression. How uneasy he feels.

Dean sucks in a sharp breath and slaps his hands down on the table, wincing as he stands up, back sore from sitting for too long. And still sore from getting thrown into a brick wall by those asshat vampires.

Cas huffs a frustrated breath and tears his eyes from Dean, sitting back in his chair in defeat.

“Alright, well, I say we head out in the morning. Let’s all get a good night's sleep; we pack up and out of here by 10 tomorrow.” Sam directs to the pair across from him, standing up and shuffling down the hall, waving good night to the pair as he walks away.

Cas is agonizingly quiet, and he stares down at the table deep in thought, teeth chewing on the inside of his cheek nervously. Dean places a hand on his boyfriend's shoulder, shaking him out of his thoughts.

“Come to bed?” Dean asks, placing a soft kiss onto his temple, rubbing his thumb in soothing circles on his shoulder.

Cas looks up at Dean with a small forced small before standing up and following him down the hall into their shared bedroom, abandoning his tea and books.

After Cas gave up his grace to be human and moved permanently into the bunker. They spent weeks shuffling around each other in the kitchen, in the hall, in the library, everywhere, before finally, Cas was the one to grow a pair and tell Dean his feelings for him. Of course, Dean already knew to some extent but was in some sort of shock hearing himself admit that he reciprocates those feelings. They spent nights together in bed, sometimes Dean’s room and sometimes Cas’s, before agreeing that it was silly for the pair to continue to shuffle between both bedrooms, and both decided that it would be best if Cas moved into Dean's room with him.

He has his own nightstand on the side of the bed along with his clothes in his own respected drawers in the dresser and his nice FBI suit, and his old trench coat in the closet. He even a few pictures and decorations littering the walls and shelves of his boyfriend's room-their room. Dean made a point to have Cas as comfortable as possible in his own space.

Cas had finally felt at home in the bunker. He felt permanent.

They both undress and change into their pajamas before making their way into the bathroom to brush their teeth together, just like every night.

It amazes Dean how fast and simple they were able to fall into routine together, him and Cas. How easy and perfect it was once Cas became human. Even when they weren’t in the bucker and stuck in some dingy motel sharing a bed with Sam just six feet away. It was always the same.

Dean always waking up before Cas and making him breakfast, them drinking coffee together in the morning. Then the day passes. They sometimes shower together and put on their nightclothes but always brushing their teeth together and making funny faces at each other in the mirror until one of them laughs so hard, spewing toothpaste everywhere. And always falling asleep in each other's arms, never letting go.

That’s their permanent routine, never faltering, until now as Dean observes Cas in the mirror, Cas not even bothering as toothpaste drips down his chin and onto his hand on the counter. Cas eyes deep, lost in thought.

Dean frowns at the sight, upset because Cas is upset about something. Something he hasn’t yet voiced to him, but Dean’s not gonna push.

They finish brushing and pad slowly to the bedroom together, laying side by side in the darkness.

Dean lays on his back, staring at the ceiling, feeling very uneasy as Cas has his back to him; he can hear Cas’s soft breathing but knows he is still awake. Dean slightly panicking over his boyfriend's cold shoulder tonight.

Cas finally turns over onto his back with a huff. His hand gropes over the bedspread before finding Dean's hand and squeezing it tightly.

“Dean.” Cas whispers.

Dean rolls over onto his side, facing Cas slowly, barely able to make out his face in the shadows of their room.

“Yeah, Cas?”

“I-I have a bad feeling about this case,” Cas admits, lips pulling into a straight line. Dean shuffles closer, lips grazing his bare shoulder.

“Why are you so worried, Cas?” Dean questions pressing his lips onto the soft skin there, fingers trailing softly up and down his arm.

“I don’t know.” Cas whimpers sadly, screwing his eyes shut and shaking his head. Dean's fingers paused, taken aback by the sudden emotions in front of him.

“Cas. It’s just a simple hunt. Everything is going to be okay. We are a good team. Nothing has brought us three apart so far.”

It’s silent for a long while after that, and Dean is almost convinced Cas has fallen asleep until he speaks up finally, voice thick with sleep and anxiety. Dean’s heart tears a bit.

“Good night, Dean,” Cas whispers into the air.

“G’night Cas.”


	2. On The Road...Again

It was way too damn early when Dean woke up the next morning. His bedside clock says it was 7:03 in the morning if he had windows in his room the sun would just be rising. Sure he got more than the four hours that he usually needs but that only left him feeling more exhausted and groggy. He hadn’t even gotten out of bed yet and he dreaded it knowing today was already going to be a long-ass day. They had an 18-hour car ride ahead of them and his back already ached at the thought of driving for that long.

He rolled over with a groan to face Cas. He was laying on his back, his chest rising and falling slowly, his lips were slightly parted and with every exhale Dean could feel his breath on his face. He didn’t have the frown on his face and didn’t have any harsh lines in between his eyebrows like he did the night before. He looked so much younger and peaceful in his sleep. Dean smiled softly at his angel.

After a few moments, he finally rolled over to get out of bed. No time for procrastination today. He made his way down the hall and saw Sam in front of the small coffee pot and the smell of bacon grease on the stove.

“Man Sammy, why don’t you make me breakfast more often?” Dean chuckled and sat down at the kitchen table facing Sammy from across the kitchen.

Sam scoffed softly, “Because if I do then you’ll start expecting it every morning. Plus, you are the ‘meat man’ right?” Sam hooked his fingers in the air and had a smirk on his face.

“You damn right I am,” Dean said as Sam slid him his cup of coffee and put a plate of bacon and eggs in front of him.

Dean sat eating his bacon and eggs thinking about everything he needed to do to get ready for the road. He needed to pack Cas and his things, they always share a bag now. He needed to make sure Baby was filled with gas and had the extra oil and essentials she needed for an extra-long road trip like this one. He needed to make sure he had any weapons they might need and then some just in case it actually isn’t a werewolf pack. You can never be too careful.He was getting anxious to get all this done and get on the road at a good time.

They sat in comfortable silence with Dean's rambled thoughts before Sam spoke up.

“How’s Cas?” He asked looking up at Dean with sad worried eyes. “He seemed pretty spooked about this case last night. What’s up with that?”

“He’s okay I think. I don’t know he didn’t say much to me about it, he was very vague.” Dean admitted, popping a piece of bacon in his mouth.

“You think he’s just anxious cause he’s not an angel anymore? I mean you have to have noticed that he hasn’t gotten into the action much since then, he mostly sticks to the research part of it.”

Dean contemplates this for a moment. Sam did have a point. Cas likes to bury himself in the research lately and only joins in on the actual hunting part if he absolutely needs to. Cas claims Dean and Sam are the ones with the _human_ fighting experience and that he won’t be much help. Dean doesn’t mind though, the less action part Cas is a part of the less he has to worry that he may get hurt.

But it is like Cas to get in his head about things and not want in on the action just cause he doesn’t have his angelic “mojo” anymore.

“Maybe..” Dean replies lost in thought.

Dean finished his plate of bacon and makes his way to the coffee pot making Cas a cup before he wakes the beast.

“I’ll get the weapon bag ready for you this time Dean. You do it every time.”

“I appreciate that man,” Dean says walking out of the kitchen and back towards his room without another word.

Cas is laying on his side now facing away from the door when Dean enters the room. He’s laying with a hand under his head making his cheeks scrunch up and all chipmunk-like. His dark hair is a mess on the pillow and he is snoring softly. Dean chuckles at the sight and sits next to his feet rubbing his hand slowly up and down his waist to slowly wake him up.

Cas hums softly and slowly bats his eyes open looking around before landing on Dean with a smile.

“Morning angel,” Dean says.

“Morning.” Cas hums stretching his arms above his head with a yawn. He looks at Dean and notices the cup in his hand. “Is that for me?” He smiles.

“Sure is sweetheart.” Dean smiles at him as Cas sits up against the headboard and takes the cup from his hands. He sighs a hum of contentment as he takes the first sip, the hot liquid sliding down his throat.

“Hmm thank you.” Cas smiles.

“No problem,” Dean says and gets up to get their shared duffle bag out of the closet. He places it on the bed beside Cas and makes his way to the dresser pulling out sets of clothes for the pair. Cas watches him and continues to sip on his coffee.

Dean packs them multiple pairs of jeans, shirts, socks, boxers, nightclothes and adds in an extra jacket for Cas cause he gets cold easily. Ya know, human things. Dean is always in charge of the clothes and Cas is always in charge of their toiletries and bathroom essentials for the pair.

Dean will never forget the time Cas packed their clothes bag and forgot underwear. Underwear! The most important part! Dean made fun of him the whole trip so much that Cas pouted and didn’t talk to him for a few hours. That never lasts long though. Needless to say, they had to go out of their way to find a store and buy some and ever since then Cas has been in charge of the bathroom supplies and he hasn’t forgotten anything since.

After a few moments of Dean packing and Cas silently sipping on his coffee, Cas speaks up.

“How long is the drive?” Cas sets his coffee cup on the nightstand and moves to sit criss cross across from Dean with his hands in his lap.

“A little under 18 hours.” Dean groans, “You can bring a blanket and a pillow for the road if you want to rest. Maybe a few books too. It’s gonna be a long day. I want to get a little more than halfway before stopping for the night.” Dean zips up the bag and grabs the small zip-up toiletries bag that they share and places that in Cas’s lap.

Cas looks up at him through his lashes. “You think you can drive that much with your back? I know it’s still bothering you, Dean. You are all stiff when you walk and bend down. You know Sam and I can drive if we take turns you won’t even have to do that much.”

Cas was right, of course, Cas is almost always right. And Dean has to admit he was getting used to Cas rubbing the sore muscles of his back every night after that last hunt, every night except for last night. So yes his back was bothering him a little more than usual today. What an old man.

“I should be fine Cas. Thank you.” Dean was grateful for his attentive boyfriend but he didn’t like it when other people dove. It was weird to him. I mean let’s be honest it’s no secret that Dean needs to work on his control issues but putting someone else behind the wheel of Baby and giving them the power to end his life in half a second is outrageous to him. It gives him the chills just thinking about it. At least if he crashes it’s his own damn fault and not someone else’s.

“Dean. Seriously get over yourself. This is exactly what got you into this position in the first place. You’re so impulsive, thinking that you can handle situations when you really can’t. God, it’s infuriating.” Cas huffs out and crosses his arms on his chest, quite dramatically. “Please let us help you.”

And so now Dean sits, seven hours later, pulling into a gas station to stretch his back and switch driving shifts with Sam. So, apparently, he lost that fight with Cas and now they have been trading driving turns every few hours. Dean thinks it’s ridiculous but it makes Cas feel better and that’s all that matters.

Dean pumps the gas as Cas and Sam make their way into the gas station for some more road snacks. They were running low before they left and wanted to get as much driving down before they stopped for their first official gas stop.

Once Sam and Cas are back out they are out of the road again and eleven hours later and all crashing into their motel beds without even bothering to change clothes too tired after an 18-hour drive. That’s one of the longest drives they have done and Dean wonders how far they would’ve made it with just him driving before he called it quits and had to pull over into a motel.

Dean and Cas fall asleep in each other’s arms that night, per usual, but now accompanied by Sams snoring four feet away from them. Dean smiles to himself as he drifts off and lets his body finally relax completely.

He loves this.

He loves his tiny family.

**Notes for the Chapter:**

> Soooo? This chapter is quite uneventful and I apologize for that. I wanted to get some extra events and details and at least part of the drive in there instead of just jumping into the actual hunt or interview parts of the story.
> 
> I hope you guys enjoyed this chapter and I can’t wait to continue writing this story for you deancas fanatics (hehe) :). 
> 
> As always kudos are appreciated and comments are even better! Let me know what you think so far!!


	3. Sleep Problems

8 MONTHS AGO

Sleep is _weird_. I mean like really unsettling to Cas since he’s been human again. He hoped this time would be easier, seeing he did have a bit of practice after the angels fell, but it’s still strange to him. How does one even get comfortable? And why does he have to count sheep?

Sleep and the REM cycle is something he will never fully understand even after the hours of research and trips to the local drug store to find ‘melatonin’ Dean had called it? Cas has even tried Benadryl, and PM cough medicine, and teas and white noise and nature sounds, but those were useless even more so. The nature sounds sent him into a mental break down, crying into his pillow one night, waking the whole bunker up. Dean showed up flying into his bedroom with a gun, thinking Cas had been attacked in his sleep, Sam standing just at the door looking helpless and sad as his brother comforted the ex-angel. Cas missed his wings. He missed flying with the birds and swimming to the deepest depths of the ocean, so the nature sounds were a no go.

After that, Dean had mentioned the stronger sleeping pills as a worst-case scenario like Valerian, Ambien, Valium, etc. the list went on and on, and it didn’t ease Cas’s anxiety when he looked up the warning signs and the possible side effects for the possible medications he could be taking in the near future. He didn’t want to have to take drugs to fall asleep. He was human now. There was nothing wrong with him. It couldn’t be that difficult, can it?

“Look, Cas, you are just overthinking it. It’s really not that difficult. You just gotta lay down and get comfortable. Maybe try some yoga? Take a hot bubble bath? You just gotta relax.” Dean says to Cas as they walk out of the CVS a few miles from the bunker. Cas carries a bag with different brands of sleeping pills, teas, and something called lavender lotion? Aromatherapy?

Dean has been kind enough to help Cas with this ‘midlife’ crisis he seems to be having, but Cas knows he can only take so much before Dean starts to get frustrated with him in the process. And again, while living with the Winchesters, Cas feels like a burden.

“I mean, how’s your bed, Cas? Are you comfortable? Do you need more pillows? A night light?”

Cas turns to Dean in the passenger seat of Baby and squints his eyes at him, “No, Dean, I do not need a night light. How _absurd_ of you to suggest that I, ex celestial being, would be afraid of the dark and need to acquire the assistance of a ‘ _night light’_ “ Cas uses air quotes during his lecture and huffs against his seat defensively.

How dare Dean and his friggin human brain, which gets plenty more sleep than he does, insult him. Cas is definitely NOT scared of the dark. That isn’t a problem.

"Cas...you're _tired_. I am just trying to help. Please don't bite my head off for caring." Dean speaks softly as he turns onto the busy street. Dean reaches over and taps Cas's knee affectionately. Cas needs to know that Dean and Sam are just here to help. And deep down, Cas does know that. But he can't help but think that he's causing more trouble than he is worth. 

Cas nods slowly, eyes on his lap as if that's where the answer to all his problems lie. 

"What are you thinking about?" Dean asks, eyes trained to the road, hands on the steering wheel. 

"Is there something wrong with me?" Cas asks softly, sad, "I mean, it's the easiest thing in the book, right? Falling asleep? So, what's my deal?" 

Dean is quiet for a long while, which only sets Cas's mind faltering even more than it was previously. There _is_ something wrong with him. Dean _thinks_ there is something wrong with him. Cas looks at Dean expectantly, waiting. 

Dean finally looks at Cas with serious emotion in his eyes, yeah Cas may not be able to read Dean's soul anymore, but he can _read_ Dean. That won't ever change. Dean is an open book to Cas, has been from the very beginning. He stares back at Dean with the same intensity.

"Cas, I need you to listen to me. There is nothing wrong with you. Nothing at all. You are a human now. Just a regular ole powerless human. You may have some sleeping issues, yeah, but I mean, who doesn't?" Dean laughs. 

"You do." Cas laughs with him. "You are the worst sleeper I know, Dean." 

* * *

Back at the bunker, Cas is even more overwhelmed than he was before if that is even possible. He has the pill bottles laid out in front of him with his laptop on his lap looking at multiple websites about the different sleeping pills he purchased earlier that afternoon. He is alone now, Dean went to his room to "unwind" so he says, and Sam is probably somewhere with his head in a bucket of research. 

Cas gives up after looking through the sites and decides to take the Ambien sleeping pill, although he is very skeptical if it will work or not, seeming as all the other drugs he's tried only works for a bit and then decides to just...stop.

He downs the pills with a glass of cold water and decides to make his way to his bedroom. He stops in front of Deans door. Should he say good night? Thank him for how helpful he has been to Cas these last few weeks? Or just ignore the fact that a deep part of him is aching to crawl in bed with the hunter and curl up beside him and fall asleep there like a kitten, head against his shoulder and all? No. Cas should definitely not do that. Cas _can't._ That would unmistakably make Dean uncomfortable and make him want to boot Cas out of the bunker-again. 

Cas walks away from Deans room. 

Now is the hard part. He doesn't know what to do now. He's alone sitting on his bed with his hands on his lap. He's lost. 

This whole transition from angel to human has been extremely difficult for Cas. And he knew it would be, no doubt about that. The eating, the sleeping-well the lack of sleeping, the showering, the _urinating._ It's all so tedious and time sensitive. But being here, with Dean and Sam. It makes all this suffering and searching for his true purpose worth it. Dean is worth it. Dean is the reason he decided to carve out his grace and tie a balloon to it, his grace soaring thousands of feet in the air like he once would himself, never to be seen again. 

There is a soft knock at his door, Cas is so engrossed in his thoughts he doesn't hear it at first, only catches the movement of the door opening and Dean poking his head in. 

"Oh, you are awake. Thought maybe you were already gone and dreaming on me." Dean laughs softly and shuts the door behind him. 

Cas's eyes follow him as Dean makes his way to sit next to Cas on the bed, feet flat on the floor in front of him with a beer in one hand. 

"Ya know, can't really get to sleep sitting up." Dean laughs nervously after a few beats of silence, Cas still watching him. 

"I was-thinking." Cas admits.

"Well, that can't be good. Penny for your thoughts, Angel?" 

Cas hesitates for a moment, debating whether he should be honest with Dean and tell him all the struggles he's had to face with becoming human again for him and hasn't talked about yet. Debating whether he should admit to Dean that he is the reason he didn't want to be an angel anymore, that he wanted to know what it's like to truly feel human emotion and grow old with his two closest best friends. Debating whether he should mention how devestatingly beautiful Dean looks right now with his hair ruffled up all askew from a long day and his shirt unbuttoned with a trace of wrinkles to it and the faint crease in between his eyebrows when he's deep in thought. 

"I don't know Dean. There's a lot of -things in my head right now that I don't quite know how to express yet."

Dean nods slightly and takes a swig of his beer, emptying it. He reaches across the bed and sets in on the bedside table. There is a framed picture of Dean, Cas and Sam on his nightstand, Dean studies it for a moment, expression unreadable. 

"Well, maybe that's the problem? You need to talk about them, whether you know how to express them or not. You know I am always here to listen to you man. You honestly haven't said too much since you have been all 'non-mojoey'."

"What do you want me to say Dean?"

" _Anything,_ man. Whatever you want to say." Dean locks eyes with Cas hard and Cas can tell that Dean means it. Whatever Cas wants to admit or throw out into the open, Dean is giving him the opportunity. Maybe this is what Cas needs, an opening. 

Cas sighs deeply and goes to turn off the overhead light and replacing it with the bedside table light from his lamp and strides back to the bed, this time under the covers to shield himself from the vulnerability he is about to hold. He lays on his back staring at the ceiling for a long while, contemplating where to start. He can feel Deans eyes on his as he waits and wonders what he is thinking. 

Cas sighs again.

"I must admit that becoming human, changing from the celestial being that I have been for so many eons has been incredibly-quiet and _lonely._ " Cas pausing taking another breath to steady himself, which is another thing he wasn't used to having to control, ugh humans. 

"I was so used to being so in tune with the earth and all of its elements and organisms. I used to know every part of every microscopic fiber. I could walk outside and hear every little detail there was and now-nothing. And it's extremely frustrating being a whole new me. A less powerful me as you will but that was a me that I knew to only be true until recently." Cas runs his hands threw his hair tugging at the roots. "And the most frustrating one?" 

Cas looks up at Dean dropping his hands to his chest. 

"I can't see your soul anymore."

Dean takes in a sharp breath holding Cas's eyes and Cas internally panic for a moment. He messed up he shouldn't of gone that far, this is why he didn't want to start this conversation tonight, knowing his exhausted ass brain would cause some stupid shit like THAT to fly out of his face. Cas internally stabs himself.

But Dean doesn't even look upset? He looks almost relieved? 

"What is that like? For you? My soul?" Dean asks timidly, like he's unsure if he's allowed to ask this question or not. 

"Your soul? Was always so light and bright. I could always pick you out the easiest in a room full of them. They all mostly look the same but yours was different. You are different Dean." Dean softly smiles at this, and sparkling slightly and Cas lets out the biggest yawn. He actually _yawns._ Not cause he's bored oh God no, not in this conversation but because he is actually relaxed and tired. 

"I can't believe it. Did you just actually yawn Cas?" Dean teases him, bumping his arm into Cas. 

Nice subject change Dean. Good one.

"I think so? We shall see how tonight goes I guess."

Deans quiet for a bit before responding to Cas. 

"Would it- would it help if I sat in here with you for a bit? Just until you fall asleep so you aren't so alone?" Dean suggests. 

"I would like that yes Dean." Cas admits, getting cozier and deeper into his covers, blankets all the way up to his chin. Dean slides off the bed onto the desk chair to give him room, folding his arms onto the bed and tucking his fists under his chin. 

"What so your are just gonna _watch_ me fall asleep?" Cas asks teasing. 

"Yes, you got any tips to share with me? I mean you were the expert in this area." 

Cas shoves Dean playfully with a laugh, "Shut up and let me sleep you old man." 

"Not as old as you." Dean bites back. 

"Good night Dean." Cas closes his eyes, contently and falls asleep. 

So maybe Dean _does_ stay a little while longer after Cas finally drops off into dreaming land but that's okay with him. He watches the angel contently before starting to drop off into sleep himself. He turns off the lamp and replaces the chair back at the desk looking back at Cas as he reaches the door.

"Good night Angel." 

**Notes for the Chapter:**

> A flashback chapter :) some Destiel fluff before they became a "couple". 
> 
> I think I will drop in some flashback chapters of Cas transitioning from angel to human and some more Destiel fluff and memories to fill in some more plot in this story. Thinking of doing it every other chapter or so but I am not positive yet. Let me know what you guys think :) 
> 
> Thanks for reading!


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